1,1'-Carbonyldiimidazole → HCID 71288110, compound

HRID 1497861Notes

Reaction equation

HRID 1497861 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[F:13][C:14]1([F:21])[CH2:17][CH:16]([C:18]([OH:20])=O)[CH2:15]1.O/[N:23]=[C:24](/[C:26]1[CH:27]=[CH:28][C:29]([CH3:40])=[C:30]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:31]=1)\[NH2:25]>CN1C(=O)CCC1>[F:21][C:14]1([F:13])[CH2:15][CH:16]([C:18]2[O:20][N:23]=[C:24]([C:26]3[CH:27]=[CH:28][C:29]([CH3:40])=[C:30]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH:31]=3)[N:25]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 137777893,3-Difluorocyclobutane-1-carboxylic acidHCID 62666076HCID 62666076, compound

Product 1

HCID 71288110HCID 71288110, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

CDI (1.2 g, 7.34 mmol) was added portion-wise to a stirred solution 3,3-difluorocyclobutanecarboxylic acid (1 g, 7.34 mmol) in NMP (10 mL). After 30 minutes, (Z)-tert-butyl 5-(N′-hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) (1.8 g, 7.34 mmol) was added in one portion and stirred for another hour at room temperature. The solution was then heated via microwave at 120° C. for 20 minutes. The solution was partitioned with EtOAc and water. The organic phase was separated, dried over MgSO4 and purified over silica gel to afford tert-butyl (5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamate (36) (1.2 g, 45% yield). MS m/z 366.1 (M+1)+.

Workup

  1. temperatureThe solution was then heated via microwave at 120° C. for 20 minutes
  2. customThe solution was partitioned with EtOAc and water
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. custompurified over silica gel

Sources & evidence

ORD record
ord-0aa5a8c29008417fb1e3a22b811c2160
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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